


Frustrated and Fabulous

by FairyNiamh



Series: Drag Queens and Ruffled Lace [2]
Category: Teen Wolf (TV)
Genre: Anal Sex, AutoAnal, Autofellatio, Crossdressing, Dirty Talk, Djinni & Genies, Drag Queens, First Kiss, First Time, Humor, Knotting, Loss of Virginity, M/M, Misunderstandings, Non-Graphic Violence, Panties, Plot What Plot/Porn Without Plot, Sex Toys, Sexual Tension
Language: English
Status: Completed
Published: 2013-06-09
Updated: 2013-06-09
Packaged: 2017-12-14 10:41:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,689
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/836012
Author URL: https://archiveofourown.org/users/FairyNiamh/pseuds/FairyNiamh
Summary: <blockquote class="userstuff">
              <p>Stiles is a frustrated virgin and he is determined to do something about it - too bad Derek Hale keeps interfering.</p>
            </blockquote>





	Frustrated and Fabulous

**Author's Note:**

> This turned out funnier than I was expecting, but I am still proud of it. Thank you to the lovely drivvenwrinth for being a fabulous beta.

Stiles walked through the room, making sure everything was shut and locked up tight. Thank fuck, his dad was working nights this week because he wanted the ability to get semi-loud if he needed to. Not that he was planning on being able to be loud, but really what kind of self-sexual exploration was it if you had to be silent for fear of being heard or worse walked in on? This was why Stiles was happy he was an only child.

Of course, he would forever have nightmares of the time his dad walked into the room when he first time figured out that touching his dick felt good, really fucking good. He had not meant to be loud then, but shit happens and overprotective sheriff dads run in where fools fear to tread. That had been the quickest his dick had ever made its retreat. It was like a pin had pricked his balloon animal. Pttthhhhbbbb.

He shook his head to clear it of such thoughts. It was time to get his mind off of bad memories like that, if he kept it up then he would never have the nerve to try everything (or anything) that he wanted to try. Once his security was no longer in question; he quickly stripped off his clothes and laid down on the bed.

He slowly worked his dick and played with his balls until he was fully erect. With, great difficulty, he stopped his ministrations and readjusted his body so his head was hanging over the edge of the bed.

Then, with more grace than he knew he had, he slid head first off of the bed until his shoulders were touching the floor and his ass was up in the air. He took a deep breath and slowly brought his feet up and then down toward the floor in front of him. He opened his mouth and stretched his neck up as his cock got closer and closer to his mouth. He didn't care if some people would think that it was pathetic that he was giving himself his first blow job. The point was he would get a blow job and know what it felt like. Besides, he would know best what felt good and what felt ‘meh’.

Just as the tip of his tongue touched the tip of his dick a loud banging rang out from his closed window. Remember what Stiles thinking about his grace? Yeah, it went out the door when he heard that noise and flailed while upside down. Of course this lead to him falling and crushing his erection into the floor when his feet and knees refused to grip the surface. Maybe he should have taken off his socks too. Whatever, the result was an instant erection killer and a very loud moan of pain, which was not the type of moaning he wanted to be doing at this moment. This of course made the knocker at his window bang harder making the noise much louder...

With great difficulty, he got up and wrapped his sheet around his nude body before slowly hobbling over to the window to reveal a semi panicked Derek at the window.

"If you or someone in the pack isn't dying, I may kill you," Stiles panted out as he shifted and winced when a jolt of pain traveled from his dick to his neck.

"You okay?" Derek asked cautiously as he ducked under the window and slid into the room.

"Oh I am just peachy keen. Derek, why are you here?" Stiles growled while still slightly doubled over.

"I wanted to tell you that we have a pack meeting tomorrow night. Seven sharp, be there," Derek said simply.

"Wait, you mean you came here, to my room, to tell me about that?" Stiles asked as his poor mind boggled at Derek's motives.

"Yes," he said simply.

"You couldn't have someone in the pack tell me at school tomorrow? Or hey, novel ideal here, texted me? If that was beyond your capabilities, how about just calling?" Stiles asked. He couldn't believe that he hurt his dick because of Derek's dick move.

"No, be there," growled before leaving through the window that had caused Stiles so much grief and pain this night.

Any thoughts of 'Stiles Happy Alone Time' followed Derek out the window. With another groan he went downstairs, unbolted the front door, turned on the porch light, and the went back upstairs to let sleep help ease the pain of his still aching penis.

It would be another month before Stiles felt brave enough to try anything other than a quick slap and tickle in the shower. Of course after the last incident he had struck 'try Autofellate' off of his list. The pain and the bruised penis hadn't been worth it. Sexual psychological damage was the worst kind to have.

Of course that didn't mean that he would stop looking at porn to try to find new things to try. That was how he discovered Autoanal. He had watched the video in awe and wondered if he could do it and if he could; was he technically taking his own virginity? Toys didn't count toward the virginity count, according to books and websites he viewed, so his own dick shouldn't. He had gotten off by spanking his monkey several times, so this should be the same, only slightly different. Well, even if it did count at least he wouldn't die an eighteen year old virgin if he snuffed it tomorrow.

Besides, this sexual tryst he had carefully planned out. Even more so than the Autofellate. He got a cloth tape measure and measured the distance between the base of his cock and his anal opening. He checked that he could indeed safely, and painlessly, tug his balls the required distance to the left (and then the right, just for knowledge you understand.) Then he set about checking the flexibility of his cock.

He moved it left, right, up, and then down. Down was the tricky one and the ultimate goal. He needed to go down to get his dick to and then into his ass. He carefully flexed it until the barest hint of pain and then released his grip.

It took him three weeks to get his dick flexible enough to barely touch the tip to his opening. He kept this regimen of flexing and added a bit of stretching to the routine. It felt odd, having his finger up his own ass, but it wasn't as unpleasant as he had anticipated. One finger swiftly turned into two fingers and then into three. By the end of the fourth week, he felt confident (and more than a little ready) to try to fuck himself.

He followed the routine of closing and locking the doors and windows, this time adding a 'do not disturb' sign to the window. Hopefully that would keep the local werewolf population from banging on his window while he was trying to enjoy his special alone time.

He stripped down and slowly worked his cock to half erect (the key to this, ‘flexibility’ in the dick department) and worked three fingers deep into his ass. Of course, this _would_ be the day that his Dad came home early and the Derek _would_ decide that he should be a civil wolf and ask to be let in the front fucking door after his father.

His father, who he thought hated Derek with all his daddy heart, let the sneaky wolfy bastard not only come inside, but directed him to go up to Stiles room. So Derek came in and caught him spread eagle, with one fist slowly jerking his cock, and three fingers jammed deep inside his ass. Yeah, his life? He fucking hated it and he was getting desperate for more than his fist.

"Derek," Stiles squeaked as he threw the covers over his nude body and sit sat up to face the Alpha head on. "What can I do for you?"

"Do you need me to come back at another time?" Derek asked slowly while blushing (just a touch.)

"No, pretty sure the mood has fled the building. What can I do for you?" Stiles asked sourly as he covered up his nudity more and sat up.

"Well, I need you to look up some information about harpies. Scott thinks there was one at the college. Wait, he said siren; was there a difference?" Derek tried to remember while looking anywhere, but at Stiles.

"Harpies screech and Sirens sing luring songs. Sirens are usually found near the ocean though. Any clue why Scott thinks this?" Stiles asked as he shimmied into his boxers under the cover. Thank fuck he had set a pair of them close by.

"Yeah, he saw this girl and all thoughts of Allison left him. He's sure he was hit with a spell or some kind of enchantment," Derek sghed.

"Or it could be hormones. She's eight months pregnant and with all the complications she's had with this pregnancy doctor said 'no sex.' I gave the idiot a pocket pussy and Allison even offered to use it on him, but does he? No, he would rather have blue balls and get random boners at pretty women than jerk off!" Stiles huffed angrily. Okay, so he was suffering from his own case of blue balls, but at least Scott had a loving partner willing to help him out. Dumb ass bastard.

"Did not need to know any of that information," Derek said dryly as he rubbed his forehead.

"Tough shit, now then let's look at the bestiary, a book that _he_ actually has access to. Let's see here; yup, we live too far from the ocean for it to be a siren and Harpies are not very good shifters. They hide their feet using pants and boots because they can't disguise them any other way, though they can enchant their wings to become invisible. Does this help?" Stiles asked sourly.

"Yeah, it means that Scott was an idiot. He was going on about her ankles, if what you said was true, I doubt he would even like her ankles much. Could you talk to him? I don't need this bullshit right now?" Derek asked while rubbing his temples.

"Yeah, sure, whatever you say," Stiles sighed.

"Good, see you around," Derek said before exiting out the door, again with the human like behavior.

Stiles looked down at his crotch through his boxer briefs. "Sorry big guy. Hopefully next time we get together things won't turn out so badly for us," he said mournfully.

After that incident Stiles figured it just wouldn't be safe for him to do anything more than a quick jackin' the beanstalk in the shower from time to time. That didn't stop him from thinking of things he would like to try or from letting his mind wander to certain places.

As a tribute to how fucked up Stiles life was; he had forgot to put his 'shut up' filter in when he went to visit the wonderful ladies at the Jungle Room.

He tried to make it to the club every other Friday because the ladies there worried about him. Especially Flora who had recently decided to adopt him as her son, much to his dad's discomfort and oddly enough satisfaction.

Of course with Flora Lee (‘the florist extraordinaire! You can call me Momma, baby boy. You are so cute and adorable’) came a few others who Stiles, rather proudly called ‘Aunt’: Miss Diagnosed ‘(because the doctors swore I was a boy when I was born’), Kee Note, (‘after all every good man needs one’), Ivana Cox (‘who doesn't want one?’), Anita Screw (‘preferably a good one, because they are so hard to find these days’), and Ima Sextoy ‘(better to have a living breathing toy than a blow up any day’). Of course they all made it their duty to make Stiles as uncomfortable and safe as possible.

They had gone out of their way and even met up with his dad and set a reasonable curfew for him on Friday nights. They also promised to keep him out of trouble and away from all alcohol, sadly they kept their promise. Bitches, the lot of them; always spoiling his fun, but he still loved them.

One Friday he was sitting there and said, quite innocently, "I wonder how it feels to wear ladies underwear." He hadn't meant to say that out loud, but he had. Much to the delight of the ladies.

They, naturally, squealed in delight and set about making him as embarrassed as they could. "You're so skinny, we'll have to pick up some at the specialty shop a few towns over. Kee, go get your tape measure. Stiles you just follow us."

Of course this meant he got manhandled into the bathroom and then had his pants pulled down as Kee brought her tape measure. "Do you have any preferences baby?" Flora asked as she measured Stiles' waist and hips.

"No," he answered in a squeaky voice. How was this his life?

"Well, you come back here in two weeks and Momma and Aunties will have a variety for you to try," Flora smiled as she pulled Stiles' pants back up and kissed his forehead before sending him home for the night. “Time for Momma and Aunties to have some grown up fun.”

Queue Stiles going home and promptly forgetting everything that had happened. His dad was just happy that he was finally coming home by midnight and figured that a woman's touch was just what Stiles needed in his life, never mind that the female influence came attached to a dick. Flora and her girls were good for Stiles and for once, he agreed with his dad.

So when Stiles returned in two weeks’ time, he was honestly surprised to be presented with a boot box full of new panties. “They're called manties dear, because some men are not comfortable with the thought of being in ladies undergarments. And they are built a little different. A bit more room up in the front.”

Stiles honestly didn't care what they were called or why they were called that. He just hoped no one he knew saw his dear ladies giving him this box. He could just imagine Danny's face or even worse... Derek's!

“Don't worry dear, everyone goes through a phase of hit or miss kinks. Though I don't think it's a kink, underwear are underwear and none of them feel very nice. I prefer commando,” Flora told him as she patted his back. “Now, you try all of those out and wear your favorite pair when you come back to us.”

“Are you sending me away already? I just got here,” Stiles whined (just a little.)

“Of course not and don't whine dear. It's unbecoming of my son to whine like a toddler. I just wanted to get that all out of the way so you could go and put them away and enjoy your evening with us.” Flora said while softly hitting Stiles shoulder.

Stiles smiled at Flora and quickly ran out to his jeep and put away his 'gift'. He would think about the implications later. Tonight he just wanted enjoy his time with his lovely ladies and leave it at that. The night was filled with laughter, being spoiled (only a little), and at the end; promises to wear the pair he liked best next time he came to visit.

One of these days he would learn how to keep his mouth shut, really he would, but that time had yet to present itself. Saturday morning rolled around and Stiles decided that he might as well face the music and see what the lovely ladies had given him. He opened the box... and then quickly closed it.

They were dirty perverts, the whole lot of them. They were surely cackling in their homes and delighting in the thoughts of Stiles’ blushing face. Thank everything under the sky and stars that they didn't make him open the box at the club.

The small bouquet of ruffled panties (rumba he later learned was the correct word.) were obviously from Momma Flora (the rose perfume and the way they were arranged like flowers was a dead giveaway.) The thongs, probably came from Ivana and Anita; both loved to talk about men in thongs. The crotchless, and there was no way he was even going to try those, were probably from Ima. The sensible cotton panties were obviously from Kee, she always had a good head on her shoulders. The satin and silk thigh highs had to be from Missy, and he would never call her that to her face because he liked his nuts where they were thank you very much.

Tossing aside the pairs of crotchless underwear, because again, no fucking way, he dug in and pulled out a string thong. “Now or never,” he muttered as he gathered up the rest of his clothes and headed to the bathroom to begin his morning ritual.

After his shower, he dried off, put on lotion (okay, so it was really sunblock – he had fair skin and burned easier than a piece of white bread in a bonfire), and then slipped on the thong panties. After much wiggling and rearranging his junk he felt confident enough to finish getting dressed and going out for the day.

First order of the day was to get a couple of dozen (read eight dozen) various donuts from the Patty Cake Bakery. Thankfully they had done this enough times (and Derek had made and paid for the order the day before) that the ladies simply come out smiling and thanking him for his business. Then off to the pack meeting with ravenous wolves and a starving pregnant lady.

Stiles fidgeted and resisted the urge to pull the underwear out of the crack of his ass. This lasted until halfway into the meeting when Stiles stood up and bolted for the downstairs bathroom. He opened the medicine cabinet while pulling down his pants. Once his pants were mid-thigh he grabbed the pair of manicure scissors and clipped the two thin strings holding the underwear up.

Thong panties were definitely not right for him. He was not up for walking around with a wedgie in his ass all the time. Hell, he didn't even think he could wear them for a short period of time to try and entice any man he might try to catch. Though maybe the wider ones would be more comfortable than the string kind.

Suddenly remembering where he was, he looked for a place where he could stash the offending garment. Thinking of nothing he rolled them into the smallest ball he could and stuffed them in his pants pocket before pulling his pants up and feeling a little self-conscious about being commando near the pack.

"I just remembered I forgot to turn off the coffee pot at home. Have a good meeting," Stiles yelled as he slipped out the door and then ran for his precious jeep. He pulled over at the rest stop on the way home and threw the thong panties away in the trash cans. Well, at least Derek hadn't caught him with his pants down, again.

Stiles went through the next few weeks trying on various underwear and trying to judge them fairly. Skipping any future adventures with the thongs and putting away the crotchless. (What? He may actually get someone to wear them for one of these days.)

The sensible underwear were comfortable and looked enough like briefs that he could wear them to Lacrosse practice. The silk and satin ones made him feel sexy... and the satin rumba panties, they not only felt fabulous, but they made his ass look wonderful. They were; by far, his favorite type.

So when it was time to go back to The Jungle he slipped on his rumba panties and a slightly larger than needed, pair of pants. The ladies greeted him with questions and demanded to know which ones he liked the best.

"Promise no hurt feelings?" Stiles asked. He truly loved each of them and did not want to hurt their feelings over underwear.

"Oh honey, we may pout and shed a few fake tears, but there is no way we are going to get our hearts broken because you didn't like a certain type of underwear. What kind of family would we be if we let such nonsense come between us?" Anita asked.

"Okay, honestly..." Stiles bit his lip and looked around making sure no one was eavesdropping on them. "I love the rumba pants the best. I did NOT try the crotchless, no one to wear them for. The thongs were a no go, I kept wanting to dig them out of my ass."

"Told you his sweet little ass would be too sensitive for those," Ivana whined gently slapping Anita's shoulder.

"And I really liked the rest too. I just... really like the lace, the feel, and the look of the rumbas." Stiles couldn't believe he was actually having this conversation in public where anyone could hear him.

“Bathroom, now,” Flora ordered as she grabbed Stiles’ arm and all but dragged him to the bathrooms. Momma may be a lady, but she was strong (or at least stronger than he was.) As they entered the bathroom she loudly said, “All you Chester’s and Molester’s out now. Flora has some business she needs to discuss and none of you losers are invited. Buh-bye now.”

Stiles had to bite his tongue to keep from laughing. Momma was over the top and everyone listened to her or they were politely asked to leave. (Meaning she would put her designer size 13s in your keister.)

"Let me see," Flora said just as soon as everyone had filed out.

"Oh, come on... no. What if someone walks in?" Stiles asked in a hushed whisper.

"Then I'll bitch slap them for peeping at my baby boy. Now, let me see your cute little ass," Flora demanded while snapping her fingers.

Stiles should have known, he should have fucking suspected that Derek Hale, creeper extraordinaire, would come into the bathroom just as his pants were down.

This led to a frenzied chain of events. Derek was yelling, his Aunts were doing their best to cover Stiles, and Flora backhanded Derek so hard; she knocked the werewolf flat on his ass.

Which was a spectacular blow, because all of Derek's Beta's put together couldn't knock Derek down and this only confirmed Stiles deep, not at all dark, suspicion that Flora was not as human as she was playing.

"Stay down kibble breath. Why in the hell were you trying to assault my son?" Flora growled as she put her impressive heel to Derek's throat.

"Son? Stiles do you know this _male_ Djinni was claiming to be your mother?" Derek growled in return, but stayed on the ground nonetheless. Evidently Sourwolf _did_ have a small sense of self preservation.

"Derek, Flora _is_ my Momma. Yes, I knew _she_ was a Djinni and my dad knows I call her Momma. Hell, he applauds the fact that there was someone to keep me busy and safe on Friday nights. Flora you can let him up. He's a creeper and very grumpy, but he wouldn't hurt me," Stiles explained. Really, his world was filled with supernatural creatures.

"I hate werewolves," Flora said as she turned her back on Derek. "How did you know what I was darling? I was very careful around you."

"They're not all bad. You should see Isaac, he's cute as a button. Makes you want to coo and pinch his cheeks when he blushes or laughs," Stiles said with a laugh.

"Shut up Stiles," Derek growled. Of course sourwolf would be protective his pups.

Stiles rolled his eyes and gave Derek a look that clearly said 'shut up'. Of course it was at this time that Stiles noticed everyone (except Derek, Flora, and of course him seemed frozen in time. "Neat trick, you'll have to teach me sometimes. Could come in handy when I am running away from crazed wolves or even more crazed hunters."

"Stiles," she said in a desperate voice. It almost sounded like she was getting ready to run and there was no way that Stiles could lose her. He had lost one mother, he wouldn't lose another.

Stiles took a deep breath and explained, "You were careful and I didn't fully grasp that you were until you tore my Alpha here a new one. You were also a little too careful. I had to change my whole speech pattern to accommodate you. You liked to slap your hand on my mouth any time you even _thought_ that I was going to use the W word. I made my mind change that word to want. Wants are okay for you to hear. Wants don't compel you to make them come true. Well, unless they are my wants. You've been leading a good clean life here -"

"You call this clean?" Derek asked as if he couldn't believe what Stiles was saying.

"She has lived a good clean life. She has been careful to avoid wishes so she wouldn't have to take the wishers life. She doesn't want to do that anymore. Am I right Momma?" Stiles asked softly.

"Granting wishes got old after the third yahoo wished for a better wife. Like the women that they married weren't good enough. I would have been thrilled to have a companion, the few times I tried, they found out what I was and then they just had to make that wish. Every death hurt." Flora explained sadly.

Stiles smiled widely before asking "Hypothetical question: if someone was to wish that you were no longer compelled to grant wishes or to kill anyone, what would happen to you?"

Flora looked at Stiles as if he had grown a second head that only spoke Klingon. Finally she laughed and bluntly said, "I don't know. I'm honestly afraid to find out. Why?"

"Because I love my Momma and I wish she no longer had to grant wishes or feel compelled to take anyone's life. I want my Momma to be her extraordinary fun loving self," Stiles said quickly before Flora or Derek could stop him.

"You stupid -" Flora started before Derek jumped in front of Stiles growling and blocked Flora from advancing any closer to the idiot teenager he was trying to protect.

"Derek," Stiles started.

"Oh, move out of the way you stupid wolf. I would never hurt my baby, no matter how stupid that stunt was," she said as she casually tossed Derek aside before smothering Stiles in a bear hug.

"Sorry," Stiles whispered from her chest. "I couldn't let you get hurt and I wanted you to be happy. You were always so cautious and holding back. I'm not saying go wild and cause trouble, but maybe loosen up now that you are in control and no longer have to follow the 'I wish' rule."

"Thank you baby boy. You are fabulous. You hear that wolf? This boy is fabulous and if you ever hurt him I will hurt you," she growled as Derek stood up and inched closer to Stiles.

"Momma, we're - I mean he - ugh, look I'm flattered that you think that I could ever land someone like Derek, but we aren't together. I just managed to reach the friend stage with him," Stiles explained with a sad little chuckle. Once or twice he had let himself fantasize about Derek and being more than just Scott's shadow, but he was a realist and wouldn't allow that to happen often.

"Uh huh. I mean it wolf. You hurt him in any way shape or form and I will slowly castrate you. It will take three years of agony for your balls to fall off. You understand me?" Flora growled. Which was disturbingly sexy to Stiles.

"Perfectly, trust me, you have nothing to worry about. Come on Stiles, time to get you home," Derek said softly before turning and walking away, presumably to head out of the club.

Momma gently pushed Stiles to follow Derek's lead. "Be careful with that one son, he's more delicate than he looks." She informed Stiles softly.

"What?" Stiles asked, confusion clearly showing on his face and heard in his tone.

"Nothing, just go. I'll see you in a few weeks. Thank you again, for being you and for letting me be me," Flora said softly as everyone and everything around them came back to life.

"Love you," Stiles said softly before giving Flora a quick kiss on her cheek and ducking out after Derek.

When he made it outside Derek was standing by his jeep scowling and growling for all the world to hear and see. "Discretion Derek, learn it, practice it, apply it," he hissed as he got near his jeep.

"I never pegged you as an exhibitionist. Something you want to tell me?" Derek asked with a raise of his eyebrow.

Stiles pursed his lips and glared at the gruff man before he finally caved in and said before starting his jeep and driving away; "Yeah, good night. Take care of yourself. Do not go back in and mess with the ladies. They are fierce."

A few days after the underwear incident Stiles walked into his room and discovered a small red rolling suitcase on his bed. He didn't need werewolf senses to know that it had come from Flora.

Stiles opened the suitcase with a smile on his face and the quickly closed it and looked around making sure no one was peeking in. Okay, so the panties he expected... the rest? 'Oh how I would love to strangle Momma right now or at least pinch her,' he thought with a nervous chuckle.

What in the world was she thinking giving him too many condoms to use in his lifetime, lubes in flavors, _flavors_ he had never imagined, and all kinds of toys.

Cuffs, beads, dildos, vibrators, _jeweled_ butt plugs, in varied colors and sizes. What in the world was she thinking? He stuffed the panties in his drawer and the 'toys' under his bed. Maybe he could forget about all of this... like any second now.

He managed to keep his curiosity at bay for two weeks (he also managed to keep his distance from a certain Alpha as well.) Still, he could try something small, a little step up from fingering. Biting his lip he reached in and pulled out the smallest of the jeweled plugs.

Red, like a ruby, like a certain man's eyes when he was upset or pulling an Alpha. Okay, he needed to stop that line of thought right now. He reached into his side table drawer and pulled out his plain lube, because he did not need to go around smelling like strawberry, chocolate, or any of the other flavors Momma had given him, before gathering his clothes and fleeing to the bathroom.

He showered quickly, dried off, and then assumed the positioned. Well, at least he hoped it was the position... it was the position that he saw in all the porn sites and gay 'how to' tutorials. He ignored his cock, he didn't want to go to school totally horned up; lubed up the small plug and slowly inserted it.

Once it was in he slowly stood up and did a small wiggle of his hips. It wasn't uncomfortable at all. Sure the metal had been a bit cold at first, but it was warming up and yeah, Stiles could do this. All the stories he had read went on and one about men wearing a plug all day and loving it. He was only shooting for a simple five hours. (Thank goodness for half days!)

He dressed and was full of confidence and a very small thread of arousal. He made it to school, smiling, greeting everyone, happy that he had a secret that none of his classmates would ever guess.

Of course his happiness turned into a small panic when he remembered he would actually have to sit down for class. It was one thing to get a bit happy in the semi privacy of his own jeep. It's quite a different tune doing it in front of your classmates. Fuckity, fuck, fuck, fuck. Why did he choose a school day to get fucking curious about toys?

Wincing, he carefully sat down on the wooden seat and had to cover his mouth to hide the gasp that wanted to escape. It - it felt so fucking good, rubbing him just the right way inside. He was in hell. He had died from pleasure overload and was in hell. Proof was that he was in school. Nightmares and Hell always had a school scene featured there.

He curled in on himself and just held his stomach. This way any moan that escaped would be thought of as a stomach cramp. (Thank goodness there were no fucking wolves in his class. If they had been; the jig would have been up and they would have been snickering at him... or worse sniffing him.)

He begged the teacher to send him to the nurse. He was grateful that the nurse used the temple thermometers, they were easy to fool. He rubbed his temples brusquely, mussed up his hair, and quickly went inside asking to be sent home.

Temperature 101.2 degrees, just enough to get her to shoo him out the door with strict orders to go home and sleep. Hopefully it was only a stomach bug, but if the fever didn't go away by the time he woke up, call his doctor, and get checked out.

He didn't know if he should whoop or cry at his acting skills. Well, whooping was out of the question, so he gave a small smile, thanked her, and went as quickly as he could to his jeep.

Stiles took a deep breath and eased himself into his seat. The bumps and jostles on the ride home sent waves of pleasure through him. It was far more intense than the ride to school and it was a miracle that he got home without getting into an accident. He knew that he was quietly moaning all the way home and the only thought he was thinking was to get to his room and maybe try a toy or two that Flora had given him.

When he arrived home and stumbled up the stairs (walking with a stiffy in tight jeans; not an activity Stiles would recommend even to his worst enemies.) He did manage to spare a moment to consider if his gifts were at all enchanted before he made it to his bedroom door and started stripping his clothes as fast as he could.

Which wasn't as fast as he wished. Why had he worn tight jeans? Was he an idiot or something? He was never wearing these accursed jeans again. When he was finally free of his jeans he drug out the suitcase and looked through it like a madman.

He was grateful that he had the forethought to properly clean the toys Flora had given to him. He spotted the suction based dildo and grabbed it up from the mess of toys. He licked the bottom and stuck it to his hard wood floor before scrambling to get some lube and finally getting on with the act.

He didn't know why, but he needed to be penetrated, and since the only thing he had was toys he could deal with it and take pleasure from himself.

Biting his lip he settled on his knees on the floor, bent over, and proceeded to tease himself by playing with the jeweled plug. He slowly pulled it out before swiftly jamming it back in. The feeling was indescribable, but it also wasn't enough.

With a growl he pulled out the plug and tossed it aside, lubed up the waiting dildo, which was only slightly larger than the plug. He positioned himself over said device of pleasure, and slowly sat, letting the toy inside tortuously slow until he could feel his bare buttocks touch the cold wooden floor.

He didn't notice (and honestly didn't care) that he was facing away from the unlocked window in his bedroom. His thoughts never strayed past the need for pleasure.

Once the toy was all the way inside, Stiles stilled and waited for his body to fully adjust to the glorious intrusion. As it started to feel good, really fucking good, having the dildo inside him; he began to slowly ride the anchored toy.

Biting his lip he adjusted his position until it struck his prostate with every move and then - and then he let his mind wander and wonder. How would it feel to ride Danny, Isaac, a stranger, or even better, the unattainable Alpha, Derek Hale?

Derek would be bigger than his current toy and would probably fuck Stiles stupid. Not that he would ever be that lucky, but this was his imagination, his fantasy, and anyone he wanted to could fuck him.

He imagined Derek pulling his head back and marking his neck, making it clear who Stiles belonged to, talking dirty, and making Stiles love every minute of delicious torture Derek dished out.

Stiles was so wrapped up in his pleasured fantasy that he never heard the tapping at the window, or indeed the window opening. He finally noticed his company when he moaned Derek's name and the man was there behind him, growling in his ears.

Stiles scrambled off of his toy and looked at Derek with wide eyes before saying; "This isn't what it looks like."

"Scott called, said he was worried about you," Derek purred as he looked at Stiles’ nude body.

"You should worry about Scott, because he's dead. The fucking zombie apocalypse will start with him. I, however, am fine. You can go now. Shoo," Stiles said as he attempted to cover his nudity with his hands. He was going to kill Scott, Derek, or maybe both of them for cock blocking him. Although here lately it had been Derek who had been doing the blocking. Yeah, Derek had to die so Stiles could fucking reach orgasm out of the damned shower.

"You moaned my name," Derek informed him as he looked at Stiles like a man in the desert looked at a glass of water.

"It was a frustrated moan, dude. Sex, I mean orgasms, I want them and you keep getting in their way!" Stiles yelled as he looked around the room for something to throw.

"How about I help you reach it instead?" Derek purred as he slowly approached Stiles.

"What? You shouldn't make offers you're not willing to follow through with. You should be above teasing," Stiles mumbled as he backed away, Derek following him step for step, until his back was against the wall.

"Who, says I'm teasing?" Derek whispered into Stiles’ ear as he leaned against Stiles’ trembling nude body.

"Derek," Stiles moaned before reaching up and pulling him forward into a searing kiss. Even if all Stiles got tonight was a kiss, it was worth it. The kiss alone would fuel his masturbation fantasies for fucking _ever_.

"Not like this," Stiles mumbled in Derek's mouth as the Derek reached down and started to stroke Stiles. "Fuck, Derek, I'm - I'm going to..." Stiles ground out as he finally came all over Derek's hand and, Jesus fuck, his leather jacket.

"Jerk wad," Stiles growled and hit Derek. "That wasn't what I wanted."

"I know," Derek whispered into Stiles ear. "But if you want more, there are a few things you should know."

"Like what a huge cocktease you are?" Stiles growled while rolling his eyes. Truly he was getting tired of being jerked with in all the wrong ways.

"I'm not a tease, but I don't put out just because a teenager is horny. I have standards and, let's be perfectly clear here, I do not want a one off. If you want me, you get me for longer than a night. If you want a one night stand, I'm out of here, because those days are over for me. Do you understand this Stiles? Do you understand what I'm offering and what I'm asking?" he asked as he slowly backed away.

Stiles squinted at the Alpha and was fairly sure that his brain has interpreted the man's words incorrectly. "Bed. No, amend that; shirt and then bed," he finally said, pushing on Derek's chest.

"What?" Confusion evident in his voice.

"Shirt,' Stiles said as he pulled Derek's shirt off and nudged him toward the bed. “I’m naked and you're not making sense. So if we are going to talk, we are going to do it where I can be comfortable."

"I see," Derek said with a smirk as he laid down across the bed, "So you're comfortable, being naked on top of me? And you accuse me of not making sense."

"Maybe," Stiles said as he crawled on top of Derek's prone body and placed his chin on the wolf's sternum. "From what I am understanding, you do not do or want one night stands."

"Right."

"But you are willing to jerk me off and walk away in spite of your own raging hard-on," Stiles said and emphasized 'hard on' by thrusting his hips down on said erection.

"Point?" Derek asked, grabbing Stiles hips to still them. He was already in hell, he didn't need to be in purgatory.

"My point was that you are a cock blocking idiot. Fuck, how long have you wanted me and why did you never pick up that I wanted you?" Stiles growled.

"Age, and you never showed interest in me. How could I know you were hot for me and not for one of my wolves? You aren't exactly up front with your emotions either."

"Sorry, let me be upfront and honest now. Derek, I really like you and would love to give us a try. I can't promise forever, but I promise to be loyal to you while we are together and I would really _really_ love it if you would fuck me already," Stiles said earnestly.

"No," Derek said evenly.

"No? Did you just get me worked up to tell me no? What the everlasting fuck? So, you've been playing me this whole time?" Stiles ranted trying his best to get off of Derek in spite of the man's firm grip on his hips.

"Stop putting words in my mouth!" Derek growled as he tightened his hold on Stiles' hips.

"Then use your words and explain Derek, because from where I am sitting, it sure looks like you are playing me," he said as he took a deep breath and did his best not to cry. He refused to cry over this, no matter how much it hurt.

"I won't fuck you Stiles," Derek said calmly. "You deserve more than just being fucked for your first time. I'll mate with you, or if you prefer; I'll make love to you. Slow, gentle, caring, wonderful love making. I would make it everything you deserve and more, because I want you to remember this night forever. I want to ruin you for any other person in the future. I want you to be mine. Do you want to be mine Stiles? Would you let me do all that to you?"

"I said I couldn't promise forever," Stiles whispered as he laid his head on Derek's chest listening to the steady calm thump of Derek's heartbeat.

"Hey, look at me," Derek placing a finger under Stiles' chin, encouraging the younger man to look at him before continuing. "I'm not asking for forever. I'm asking for you to give me a chance at changing your mind. I don't expect it to change overnight. Hell, it will probably take months, if not years, and I am willing to pursue you that long. As long as you give me permission to try and for you to not expect me to be anything more than what I am."

"We're going to get into fights," Stiles said with a sigh.

"More than likely. So, will you give me a chance?" Derek said with a small smile playing on his lips.

"Yeah, you get your chance. Just - just don't judge me, it's my first time you know," Stiles said nervously.

"I know, and that was why it was special to me. Now, on your back," Derek said softly.

"Are you ever going to get naked?" Stiles asked with a nervous chuckle as he positioned himself on his back, his heart racing a mile a minute.

"Soon. Just lay back and enjoy yourself," Derek whispered before leaning in, soundly kissing Stiles breath away, and running his hands lazily over Stiles naked body. Making sure to never touch the one spot that Stiles actually wanted him to.

Stiles gasped when Derek left his mouth and attached his mouth to Stiles' nipple. He didn't know he was so sensitive there. "So responsive," Derek murmured blowing on his wet nipple before giving the same attention on Stiles other nipple. Combined with the fact the Derek still hadn’tt stilled his hands and poor Stiles' mind was going into overload.

"Please, please -” he begged thrusting his hips into the air trying to get Derek to take the hint and just, do something already.

"Shhh, not yet, let me enjoy myself," Derek said with a small smile (and Stiles swore that the fucker chuckled at his discomfort.) He finally left Stiles’ chest and let Stiles discovered how much better, and torturous, it felt to have Derek's mouth on his hip bone. How was it even possible to be sensitive there? It didn't matter though, it felt like heaven. Stiles imagined Derek's hot mouth on other places and all he could do was moan loudly and open his legs a bit wider encouraging Derek to explore the rest of Stiles unmapped body.

"Where's the lube?" Derek asked as he slowly and gently scratched at Stiles' perineum.

Stiles reached under his pillow, grabbed the waiting bottle, and silently thrust it into Derek's waiting hand.

Derek quickly lubed up his finger and plunged two fingers into Stiles’ slick opening causing the younger man to moan louder and bear down on the intrusion. It felt so different than his own fingers or anything else he had tried. Derek slowly moved them in and out and deliberately jabbed at Stiles' prostate driving him to near tears.

"More, please Derek, more," he begged because he truly needed more.

"Look at you so wanton and wanting. You look beautiful like this and you sound even better. You're tight, I can imagine that you'll feel like heaven wrapped around my cock. You want that Stiles? Come on, tell me what I want to hear. You know what I need to hear," Derek said as he folded a third finger into place.

"Oh, fucking hell, fuck me Derek, please fuck me," Stiles babbled as his prostate was put through the most exquisite of tortures.

"Try again Stiles. I told you that fucking would not be on the table tonight. So, what do you think I want to hear to make me take your virginity away?"

"Knot me?" Stiles gasped.

"I'll do that, but those aren't the words I want to hear," Derek sing-songed as he increased the pace of his fingers.

Stiles gasped and closed his eyes tightly to try and figure out what Derek could possibly want to hear. Fucking possessive bastard was a sadi- wait; that was it. "Make me yours Derek. Mate me and show me who I belong to, who you belong to."

Derek purred (and dogs are not supposed to fucking purr. So why was Derek purring?), removed his fingers, and quickly stripped his pants off.

Stiles gasped as he saw Derek's straining erection. Never before had he seen a more beautiful sight and he couldn't help but to salivate at the sight. "Turn over," Derek ordered.

"No, I want to look in your eyes. Take me like this. You can do that can't you? Or was there a rule saying werewolves can only have doggy-style sex?" Stiles asked with a smirk, spreading his legs as wide as they could go in an obvious invitation.

"One of these days that mouth was going to get you into trouble," Derek replied with a smirk of his own as he coated his erection and lined up to take Stiles. "The other way would have been easier on you." He informed Stiles as he slowly pushed his way in.

"Trust me," Stiles panted; "No complaints about any of this from my side of the court. Oh, holy hell, so fucking big. I can't believe you're actually in me."

"Tight," Derek said through gritted teeth as he pushed his way into his willing mate. He had been right, being inside Stiles was like heaven.

"Oh sweet mother of pearl, fuck. So big, so perfect," Stiles muttered, tightening his legs around Derek's waist as he felt his Alpha's balls brush up against his bare ass. Once fully seated deep within Stiles, Derek paused and they both took a minute to gather their wits and breathe. It wasn't that long before Stiles was softly telling Derek to move his lazy ass.

The slow and lazy thrusts and the near constant brush of Derek's cock against his prostate had him breathing hard and seeing stars. He was fairly positive that his vocabulary had dropped and his IQ had diminished to Scott's level. It was worth it, all of this, every growl, every possessive utter of the word ‘mine’, every gasp for air made Stiles feel alive, wanted, and perfect. There was no way he would trade this feeling for anything.

"Close," he warned Derek. "Come on, make me come, mark me."

Derek growled and sped up until it was a near a wild animal's pace. "Shit yeah, fucking knot me!" Stiles cried. Of course he thought that werewolf knotting was a myth. None of the other wolves had one (so not his fault that he had changed in the dressing room with all of the other male members of his pack.) So you can imagine his surprise when he felt something large bump against his aching rim stretching him further with each thrust.

"Almost there," Derek warned and with one final harsh thrust he was all the way inside Stiles (including his knot.) Heaven on earth, Derek had found it in the arms of his mate. He wrapped his hand around Stiles neglected erection and pumped in time with his shallow thrusts. It only took a few more times before they were both howling in completion.

"Well," Stiles panted. "That wasn't exactly what I was expecting, but I approve wholeheartedly and request that we put in a repeat performance as soon as humanly, and wolfy, possible. By the way, why do you have a knot when the others are lacking? I play Lacrosse with more than half of them and have seen them in the shower room and have walked in on Scott more than once, sadly. No knot has been seen before yours and how long are we going to be tied together?" Stiles said while tiredly running his fingers over Derek's sweaty back.

"I was born a werewolf. So, I have a few more perks than they do. Don't know how long we'll be tied together, I have never knotted anyone before you. Sleep now. We'll go over everything in the morning," Derek said as he snuggled into Stiles waiting for his knot to go down. Stiles didn't know it yet, but there was no way that Derek could even think of giving him up anytime soon. He would fight anything and everything to keep his mate at his side where he belonged forever.

~Fin~

**Works inspired by this one:**

  * [[Podfic] Frustrated and Fabulous](https://archiveofourown.org/works/3129995) by [RsCreighton](https://archiveofourown.org/users/RsCreighton/pseuds/RsCreighton)




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